Are you craving a spooky adventure? Looking for a town with ghosts, goblins, and some spooky tales? The attractions in Sleepy Hollow, NY hold it all while bringing one of the classic horror stories, The Headless Horseman, to life. Of course, there are other things to do in town that are not quite as spooky, and we think it is all worth visiting!
Sleepy Hollow, NY is a quaint town that was the inspiration for Washington Irving’s story The Legend of Sleepy Hollow, released in 1820. “The Legend of Sleepy Hollow”, for those of you who are not familiar with it, tells the story of Ichabod Crane and his attempts to win the heart of Katrina Van Tassel.
Perhaps one of the most well-known characters in the story is the Headless Horseman who spends his days hunting for his head. I would recommend looking into the story or refreshing yourself before heading out to Sleepy Hollow. Anyways, now on to all this little village has to offer…
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Attractions in Sleepy Hollow, NY
Visit the Sleepy Hollow Cemetery
The Sleepy Hollow Cemetery is the final resting place of Washington Irving and also home to the Headless Horseman Bridge replica. Other notable burials in the Sleepy Hollow Cemetery are Andrew Carnegie and William Rockefeller.
One of the highlights for us when visiting this area was the Headless Horseman Bridge replica. About a half-mile upstream from where the bridge that played a role in the writing of Irving’s story sits the small, wooden bridge crossing the Pocantico River.
Special tours are held in select months throughout the year. You can also tour the cemetery on your own between 8:30am and 4:30pm daily.
Visit the Old Dutch Church Burying Grounds
The Old Dutch Church and Burying Grounds are the ones famously featured in “The Legend of Sleepy Hollow”. The Old Dutch Church is also one of the oldest churches in the state. The church is still active today, and outside of October is rarely open for visitation by the public. If visiting, be respectful of any regular services or events taking place.
In the month of October the church offers live readings/shows of “The Legend of Sleepy Hollow” with tours of the church and burying grounds. Year-round you can walk the grounds outside of the church and burying grounds. It will feel like the pages of the story are coming to life!
Attractions in Sleepy Hollow, NY: Visit the Phillipsburg Manor
The Phillipsburg Manor is a 1750 English manor that once housed African slaves. The Manor is a restored 18th-century farm and trading center that sits along the Pocantico River and offers interactive exhibits, historic buildings, and beautiful grounds to explore.
Costumed interpreters offer demonstrations of traditional crafts, farming techniques, and daily activities that would have taken place more than 250 years ago.For families who love being outdoors, you can stroll along the scenic pathways, watch the water-powered gristmill in action, and enjoy views of the river and surrounding landscape.
During the summer, special events take place on Saturdays with family-friendly activities, music, dancing, and storytelling. In October the manor transforms into a haunted house-Headless Horseman Hollow. Unfortunately when we visited this event was not going on, we missed it by a day!
Visit the site of the Headless Horseman Bridge
While the Sleepy Hollow Cemetery is home to a replica of the Headless Horseman Bridge, it is not where the original bridge stood. While the original bridge that was the inspiration for Irving’s story is not longer standing, you can still visit the site where it stood.
A concrete bridge was constructed where the Headless Horseman Bridge previously sat in 1912. There is a sign marking it’s location, not to far from the Old Dutch Burying Grounds. Simply take the less than a minute walk and you will come upon the sign that marks the spot.
Stop for a photo of the Headless Horseman Statue
Sitting in the center of Sleepy Hollow is the Headless Horseman Statue. You will need to be careful with this stop as it sits in the center of a busy highway. The 18 foot tall statue represents the Headless Horseman chasing Ichabod Crane. It was designed by local artist Linda Perlmutter and revealed in 2006.
It is only a couple minutes walk from the Old Dutch Burying Ground, so after visiting the site of the original Headless Horseman bridge, continue and you will shortly find the statue.
Attractions in Sleepy Hollow, NY: Visit Sunnyside
Sunnyside is the cottage-like home of “The Legend of Sleepy Hollow’s” author Washington Irving. The home itself is a beauty to look at, and it is situated right along the Hudson River, giving you some stunning views. It is located in Tarrytown, only about a mile from downtown Sleepy Hollow.
Aside from visiting and touring the house, you can also enjoy walking the trails on the grounds surrounding the home. The grounds feature paved walking trails, colorful gardens, and open lawns. Interpretive signs can also be found around the property, highlighting the history of the area.
Timed tours are offered daily during the warmer months and, like many other locations in Sleepy Hollow, Sunnyside offers special Halloween themed events in the month of October.
Shop Along Main Street
In nearby Tarrytown, check out Main Street for some local shopping and dining opportunities. The area has a small town, historic Hudson Valley village feel, which is reason enough to stop here. The street is lined with local shops offering unique and homemade products and souvenirs.
You can also find local restaurants along Main Street. You can find restaurants featuring a variety of food types, including Tapas, Sushi, Mediterranean food, pub food, pizza, Thai , Mexican, and more. You can also find bakeries and cafes. Exploring Main Street in Tarrytown is a great way to spend a slow afternoon in a gorgeous shopping setting.
Visit the Tarrytown Music Hall
The Tarrytown Music Hall has a rich history and is now believed by many to be haunted. The Music Hall was built in 1885 and has served as an entertainment venue for some of the village’s most famous residents, including the Rockefellers. It has also served as a venue for several national causes, served as a movie theater, and now as a performing arts center.
The Music Hall is also believed to be haunted and ghost tours/paranormal investigations are offered on select days.
Visit the Sleepy Hollow Pumpkin Blaze
The Sleepy Hollow Pumpkin Blaze is one of the best attractions in Sleepy Hollow, NY if visiting during the fall months. The pumpkin blaze features over 7,000 pumpkins that are lit up. The event takes place at the Van Cortlandt Manor, a 17th century Manor built near the confluence of the Croton and Hudson Rivers.
A timed ticket will get you entry to the festival, where you can see a wide display of pumpkin carvings and structures, including a working carousel, the Headless Horseman, a pumpkin tunnel, and a bridge made out of pumpkins.
Attractions in Sleepy Hollow, NY For Outdoor Lovers
Visit the Sleepy Hollow Lighthouse
The Sleepy Hollow Lighthouse, built in 1883, sits inside Kingsland Point Park. The park itself is a nice place to visit and enjoy a relaxing afternoon with great views of the Hudson River and the Tappan Zee Bridge.
The park has a small area of water access as well, but the sand was littered with debris when we visited (Don’t forget to follow the Leave No Trace Principles wherever you go!). There is plenty of parking and from there you will take the short, five-minute walk over to the lighthouse.
The lighthouse itself is rather small, but it is still worth the trip. The path from the park leads right up to the bridge that you can cross and come right to the foot of the lighthouse.
Visit the Rockefeller State Park Preserve
The Rockefeller State Park Preserve is a 1,400 acre nature preserve only about a mile from Sleepy Hollow. The park offers visitors a chance to get away from the traditional attractions in Sleepy Hollow, NY and explore the natural beauty of the area.
Hiking is one of the best things to do, with over 45 miles of old carriage roads and trails. The Rockwood Hall Trail is one of the best at 2.4 miles round trip with an elevation gain of 167 feet. Along the hike you will be treated to views of the Hudson River and the Palisades Cliffs.
Brother’s Path is another excellent option at 1.4 miles round trip. The flat, old carriage roads takes you around Swan Lake and past the iconic “Rockefeller Teeth” stone boundary markers. The trail has an elevation gain of only about 40 ft. and is stroller friendly.
Other activities in the park include bird watching, picnicking, sledding, cross country skiing, and snowshoeing in the winter.
Attractions in Sleepy Hollow, NY: Stroll the Sleepy Hollow Riverwalk
The Sleepy Hollow Riverwalk is one of the best outdoor attractions in Sleepy Hollow, NY. The Riverwalk stretches along the edge of the Hudson River, connecting parks, historic sites, and public spaces throughout Sleepy Hollow and neighboring communities. The Riverwalk is still in progress, with portions of it still in development. Once completed, the Riverwalk will span 51.5 miles.
The portion of the Riverwalk that is open in Tarrytown/Sleepy Hollow passes some of the most popular attractions in Sleepy Hollow, Ny including the Sleepy Hollow Cemetery, the Old Dutch Church, the Phillipsburg Manor, Kingsland Point County Park, and the Sleepy Hollow Lighthouse.
Another section takes you along the scenic Hudson Riverwalk Park and Pierson Park. Along the route the trail is made up of paved and unpaved paths, promenades, and sidewalks.
Visit the Croton Gorge Park
Croton Gorge Park is another excellent option for an outdoor adventure when visiting Sleepy Hollow, New York. The park is about a 20-25 minute drive from Sleepy Hollow and takes you to the 97-acre park that sits at the base of the Croton Dam.
The Old Croton Dam was built in 1842 to supply New York City with water. The dam was replaced in 1907 by the New Croton Dam (Cornell Dam) to keep up with the growing city’s needs. Today you can visit the dam, walk across the bridge that spans the Croton River, and access hiking trails within the park.
One of the best trails in the park is the one that takes you to the base of the New Croton Dam. The trail is 2 miles round trip and takes you up the almost 300 ft. stone dam to the pedestrian bridge that overlooks the falls, dam, and reservoir. You can also access the Old Croton Aqueduct Trail here.
Other activities in the park include picnicking, cross-country skiing, and sledding in the winter. You can also view the waterfall tumbling down the rocks beside the dam.
Walk the Old Croton Aqueduct Trail
The Old Croton Aqueduct Trail is a 26 mile trail that starts in the Croton Gorge Park and runs across Westchester County into Yonkers and New York City. When visiting the area with kids, you can choose just to hike a portion of the trail closer to Croton Gorge Park.
The Old Croton Aqueduct Trail passes by several attractions in Sleepy Hollow, NY along with the surrounding communities. These include the Van Cortlandt Manor, Croton Point Park, the Phillipsburg Manor, the Sleepy Hollow Cemetery, the Old Dutch Church, and Sunnyside.
The Old Croton Aqueduct Trail is wide and mostly flat, making it a good hiking option for families.
Frequently Asked Questions
Is Sleepy Hollow worth visiting with kids?
Yes! While Sleepy Hollow is famous for its spooky legends, it’s also a family-friendly destination with historic sites, outdoor attractions, scenic river views, hiking trails, and seasonal events that appeal to children of all ages.
How many days do you need in Sleepy Hollow with kids?
1-2 days in Sleepy Hollow will allow you to see the main attractions. If you are looking to visit some of the parks and do some hiking, at least 3-5 days is recommended.
Is Sleepy Hollow scary for young children?
Most attractions are not scary and are appropriate for families. However, some seasonal Halloween events are designed to be spooky and may be too intense for younger or sensitive children. Make sure you check age recommendations before purchasing tickets.
What is the best time of year to visit Sleepy Hollow?
Sleepy Hollow is one of the most popular Halloween Destinations in the state, making fall the best time to visit. This is the time when special events and festivals are going on, and the scenery is enhanced by fall foliage.
Is Sleepy Hollow walkable for families?
The downtown areas of Sleepy Hollow and Tarrytown are walkable, but some of the main attractions are spread out and require a car to get to.
How far is Sleepy Hollow from New York City?
Sleepy Hollow is about 30 miles north of New York City and can be reached by car in about 40–60 minutes or by train from Grand Central Terminal in approximately 40 minutes.
***The Navigating Mom (and this post) may contain affiliate links. If you purchase from one of these links, we may receive a small commission at no additional cost to you.****
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